Methanol → HCID 20273174、化合物

HRID 371500ノート

反応式

HRID 371500 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O-])(=[O:28])[CH3:27].[Na+].[H][H].CO>C(OC(=O)C)(=O)C.[Ni].CCOCC>[C:26]([NH:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)[CH:19]=1)(=[O:28])[CH3:27]

参加物

8

反応物 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 133247163-(5-Benzyloxy-1-indolinyl)benzonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 20273174HCID 20273174、化合物収率 86.8%

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 3283Diethyl Ether溶媒HCID 7918Acetic Anhydride溶媒

実験手順

A solution of 1.52 g (4.7 mmole) of 3-(5-benzyloxy-1-indolinyl)benzonitrile of Example 18b in 60 ml acetic anhydride over 0.2 g Raney Nickel (#28 finely divided) and 0.76 g (9.3 mmole, 2 equivalents) sodium acetate was shaken at 50° C. under 50 psi of hydrogen until gas uptake had ceased and TLC analysis showed the reduction to be complete. The catalyst was filtered on a pad of celite and the filtrate was partitioned between chloroform (40 ml) and water (400 ml) and the combined organic portions were washed twice with water (600 ml), aqueous NaHCO3 (two 600 ml portions) and brine, dried over Na2SO4, and concentrated to give an oil. Chromatography on silica gel (80 g) using 1-5% methanol in ether afforded 1.31 g (86.8%) of N-Acetyl-3-(5-benzyloxy-1-indolinyl)benzenemethanamine as an oil.

後処理

  1. filtrationThe catalyst was filtered on a pad of celite
  2. customthe filtrate was partitioned between chloroform (40 ml) and water (400 ml)
  3. washthe combined organic portions were washed twice with water (600 ml), aqueous NaHCO3 (two 600 ml portions) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give an oil

出典と根拠

ORDレコード
ord-43eb213be6e2443297b393de5e2cb073
出典データセット
uspto-grants-1985_07
特許番号
US04532333

反応ノート

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